Jay Z

Long before he decided to partner with Barneys for this year’s holiday collection, Mr. Carter cut his teeth in the fashion world by cofounding Rocawear back in 1999. The brand, which was later sold to Iconix Brand Group for $204 million, sells everything from men’s clothing to outerwear to sunglasses. The guy obviously knows what he’s doing—the priciest item in his upcoming line is a watch that costs $17,900.